Went to Greece in Aug 1988 and loved it. We travelled out to the islands by ferry and it was just ok. The islands were packed and finding lodging was difficult. First island we stopped at we ended up sleeping in someones home on the floor. That was Sifnos. Next island was Milos and we had a great time there. As far as cruises go, my wife and I are going on Windstar in June, departing Istanbul and finishing in Athens. This will be our second Windstar cruise, the first one being in Tahiti. Things we liked about it were 150 pax. Nothing like the super cruise ships with 5000 pax on them. You got to know the other travellers which made the time on board enjoyable. This cruise stops at a few ports in Turkey and a few of the islands. Expect crowds in the summer and warm to hot temps. As far as what to do, it has been awhile since I have been there. We plan on touring the islands and relaxing on the beaches. If you have not travelled by mid June I will give you a report when I get back if you want one.
We rented a sailboat in 02, last two weeks of June, and sailed around the Ionian Sea (west coast). Liked it so much we did it again in 03, same two weeks. I'm a novice sailor, but this sailing was easy, no currents or tides and never more than 20 knots of wind. We rented through a flotilla program (sailingholidays.com) which is a U.K. based company (was based in England at the time) but there are others like Moorings and Sunsail. They provide a lead boat for a flotilla of around 6-10 boats. The lead crew organized everything, get you started each morning and meet you in the afternoon. Each day you are on your own then the group meets up at a new island in the afternoon. Once they see you can handle the boat they'll let you go on your own if you so choose. If you don't sail, most of the companies will provide a captian for extra $$. As far as timing, the last two weeks of June were great as Europe starts their summer holiday in July and prices skyrocket as do crowds. Weather was great and the locals were some of the friendliest folks we dealt with in ten years of taking vactions while stationed in Europe. Sailed right by the island where the sirens sang to Homer, turns out you can still hear them, they sound just like a beer can opening.
I took a greek isles cruise many years ago. Now, im forgetting what the company was called. It was on a large sailing ship, not the windjammer guys, but another. The boat was called "star flyer" if i remember correctly. The boat only had around 100 folks on it, mostly german tourists from what I can remember. We had a great time, started in kusadasi (sp?), sailed around to rhodes, mykinos, santorini, and some others. Santorini was my favorite. I remember riding donkeys down the side of the cliff with a huge dropoff, coulnt get my donkey to slow down, I was afraid. It was at least a couple hundred feet of a fall with no barriers. Waters in the areas around the islands were crystal clear. It was great and I recommend it highly. Try to hit up Istanbul on the way home. We stayed in a four-seasons, or maybe it was The Regent? Anyrate, it was an old prison that was transformed into this lavish hotel. Pretty cool. All within walking distance to the blue mosque, hagia sofia, etc.
Try Windstar curises. You can't have a better time. They do Athens to Istanbul and reverse. Been on 20 cruises and I would rate them as one of my favorites.
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